Cyclohexanone oxime

Cyclohexanone oxime
Identifiers
CAS Number	100-64-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL137035;
ChemSpider	7236;
ECHA InfoCard	100.002.613
EC Number	202-874-0;
PubChem CID	7517;
UNII	2U60L00CGF ;
UN number	2811
CompTox Dashboard (EPA)	DTXSID4021842 ;
	InChI InChI=1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 Key: VEZUQRBDRNJBJY-UHFFFAOYSA-N; InChI=1/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2 Key: VEZUQRBDRNJBJY-UHFFFAOYAH;
	SMILES C1CCC(=NO)CC1;
Properties
Chemical formula	C6H11NO
Molar mass	113.16 g/mol
Appearance	white solid
Melting point	88 to 91 °C (190 to 196 °F; 361 to 364 K)
Boiling point	204 to 206 °C (399 to 403 °F; 477 to 479 K)
Solubility in water	16 g/kg (in water)
Magnetic susceptibility (χ)	-71.52·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H228, H302, H319, H373, H412
GHS precautionary statements	P210, P240, P241, P260, P264, P270, P273, P280, P301+312, P305+351+338, P314, P330, P337+313, P370+378, P501
Flash point	110 °C (230 °F; 383 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.

Preparation

Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:[1]

C₅H₁₀CO + H₂NOH → C₅H₁₀C=NOH + H₂O

Alternatively, another industrial route involves the reaction of cyclohexane with nitrosyl chloride, which is a free radical reaction. This method is advantageous as cyclohexane is much cheaper than cyclohexanone.

Reactions

The most famous and commercially important reaction of cyclohexanone oxime is its Beckmann rearrangement yielding ε-caprolactam:

This reaction is catalyzed by sulfuric acid,[1] but industrial scale reactions use solid acids.[2]

Typical of oximes, the compound can be reduced by sodium amalgam gives cyclohexylamine.[3] It can also be hydrolyzed with acetic acid to give back cyclohexanone.

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References

J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. doi:10.15227/orgsyn.019.0020
Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308. doi:10.1016/S0920-5861(97)81500-1
W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58.doi:10.15227/orgsyn.011.0058

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[Eck-1] J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. doi:10.15227/orgsyn.019.0020

[2] Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308. doi:10.1016/S0920-5861(97)81500-1

[3] W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58.doi:10.15227/orgsyn.011.0058